Synthesis of 6H-dibenzo[b,d]pyran-6-ones using the inverse electron demand Diels-Alder reaction.

  title={Synthesis of 6H-dibenzo[b,d]pyran-6-ones using the inverse electron demand Diels-Alder reaction.},
  author={I. Pottie and Penchal Reddy Nandaluru and Wendy L. Benoit and David O. Miller and Louise N Dawe and G. Bodwell},
  journal={The Journal of organic chemistry},
  volume={76 21},
A set of coumarin-fused electron-deficient 1,3-dienes was synthesized, which differ in the nature of the electron-withdrawing group (EWG) at the terminus of the diene unit and (when EWG = CO(2)Me) the nature and position of substituents. These dienes reacted with the enamine derived from cyclopentanone and pyrrolidine to afford the corresponding cyclopenteno-fused 6H-dibenzo[b,d]pyran-6-ones, most likely via a domino inverse electron demand Diels-Alder (IEDDA)/elimination/transfer hydrogenation… Expand
35 Citations
Efficient syntheses of novel indeno[1,2-b]chromenone derivatives via hetero-Diels-Alder reactions of 2-(arylmethylene)-1H-indene-1,3(2H)-diones with enaminones
Abstract Efficient syntheses of novel 10-aryl-5 a -(arylamino)-9-hydroxy-5 a ,6,7,8-tetrahydroindeno[1,2- b ]chromen-11(10 H )-one derivatives has been reported by [4+2] cycloaddition reactions ofExpand
Multicomponent synthesis of 6H-dibenzo[b,d]pyran-6-ones and a total synthesis of cannabinol.
A multicomponent domino reaction that affords 6H-dibenzo[b,d]pyran-6-ones is reported, and the yields are considerably better than those obtained using a stepwise process. Expand
Application of dimedone enamines as dienophiles: stereoselective synthesis of amino enols of fused uracils containing a sugar moiety by hetero-Diels–Alder reactions of barbituric acid 5-ylidene alditols with dimedone enamines
Abstract Dimedone enamines were applied for the first time as new dienophiles in hetero-Diels–Alder reactions with inverse electron demand. Cycloadditions of barbituric acid 5-ylidene alditols withExpand
A metal-free one-pot synthesis of benzo[c]chromen-6-ones from 3,4-dichlorocoumarins and butadienes using tandem photo-thermal-photo reactions.
An efficient, simple and versatile synthesis of biologically valuable benzo[c]chromen-6-ones is achieved using a tandem photo-thermal-photo reaction sequence starting from 3,4-dichlorocoumarins and aExpand
Rh(III)-catalyzed oxidative C-H bond arylation with hydroquinones: sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones.
An efficient Rh(III)-catalyzed C-H bond arylation with phenol derivatives was developed for the direct and sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]p Pyran- 6-ones, giving the products in good yields with excellent chemoselectivity. Expand
V-shaped bis-coumarins: synthesis and optical properties.
A highly efficient procedure for the synthesis of bis-coumarins fused at the pyranone ring has been developed, and compounds with four structurally unique skeletons have been obtained and have been shown to strongly absorb in the violet, blue, and/or green regions of the visible spectrum. Expand
Oxidant-free, three-component synthesis of 7-amino-6H-benzo[c]chromen-6-ones under green conditions
An oxidant-free three-component synthesis of biologically significant 7-amino-6H-benzo[c]chromen-6-ones was established involving a Sc(OTf)3 catalyzed three-component reaction between primary amines,Expand
Regioselectivity of the intramolecular biaryl coupling reaction of 3-substituted phenyl 2-iodobenzoate using a palladium reagent
This study investigated the regioselectivity of the intramolecular coupling reaction of the phenyl benzoate derivative which possesses a methyl or methoxy group at the meta-position of the phenoxyExpand
Regiospecific inverse electron demand Diels–Alder reactions of 7-methylcoumarin-4-azadienes
Condensation of 7-methylcoumarin-4-carbaldehyde with different anilines affords 7-methylcoumarin-4-azadienes. The 7-methylcoumarin-4-azadienes do not undergo normal electron demand Diels–AlderExpand
Syntheses of Benzo[c]Chromen-6-ones by Palladium Catalyzed C–H Bond Activation using Diazonium Salts
An efficient palladium catalyzed C-H bond activation for the synthesis of benzo[c]chromen-6-ones using diazonium salts is described, prepared in excellent yields through two different methods. Expand


Synthesis of 6H-dibenzo[b,d]pyran-6-ones from aryl 3-bromopropenoates via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction.
Various kinds of 6H-dibenzo[b,d]pyran-6-ones 4 were synthesized via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction of aryl 3-bromopropenoates 1, in which theExpand
Synthesis of 6H-dibenzo[b,d]pyran-6-ones via dienone-phenol rearrangements of spiro[2,5-cyclohexadiene-1,1′(3′H)-isobenzofuran]-3′-ones
Abstract A series of spiro[2,5-cyclohexadiene-1,1′(3′ H )-isobenzofuran]-3′-ones were prepared from metalled benzamides and 4,4-dimethoxycyclohexadienone. Rearrangement of these spirodienones under aExpand
Synthesis of dibenzo[b,d]pyran-6-ones based on [3 + 3] cyclizations of 1,3-bis(silyl enol ethers) with 3-silyloxy-2-en-1-ones.
Functionalized dibenzo[b,d]pyran-6-ones were prepared by formal [3 + 3] cyclization of 3-silyloxy-2-en-1-ones or 1,1-diacetylcyclopropane to give functionalized salicylates, Suzuki cross-coupling reactions of the corresponding triflates, and subsequent BBr3-mediated lactonization. Expand
Electron deficient dienes I. Normal and inverse electron demand Diels-Alder reaction of the same carbon skeleton
Abstract The synthesis of compound 11 , which features a diene moiety bearing electron withdrawing groups at the 1 and 3 positions, and its completely regioselective inverse electron demandExpand
Sequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo[b,d]pyran-6-ones related to ellagic acid
A general regiospecific synthesis of dibenzo[b,d]pyran-6-one derivatives 1a,c and 8a-i related to ellagic acid is described (Scheme I, Table I). The sequence involves directed orthoExpand
3-nitrocoumarins as dienophiles in the Diels-Alder reaction in water. An approach to the synthesis of nitrotetrahydrobenzo[c]chromenones and dihydrodibenzo[b,d]furans.
The cycloadditions of hydroxy-3-nitrocoumarins 1c, 5, and 6 with 1,3-diene 9 did not work in water or in organic solvent, but did work under solventless conditions. Expand
Aktivierte Chinone: regiospezifische Synthesen von substituierten Dibenzo [b, d]pyran-6-onen und Benzo [b]naphtho [d]pyran-6-onen
Activated Quinones: Regiospecific Syntheses of Substituted Dibenzo [b, d]pyran-6-ones and Benzo[b]naphtho [d]pyran-6-ones The reaction of 2-methoxycarbonyl-1, 4-benzoquinone (1) withExpand
Bu3SnH mediated oxidative radical cyclisations: synthesis of 6H-benzo[c]chromen-6-ones
Attempts to synthesise 6H-benzo[c]chromen-6-ones by Bu3SnH mediated cyclisation of o-(benzoyl)aryl radicals failed because of the preferred trans conformation of the ester. This problem was overcomeExpand
Electron-deficient dienes. 5. An inverse-electron-demand Diels-Alder approach to 2-substituted 4-methoxyxanthones and 3,4-dimethoxyxanthones.
Several 4-methoxyxanthones and 3,4-dimethoxyxanthones were synthesized in good yield via inverse-electron-demand Diels-Alder (IEDDA) driven domino reactions between a series of electron-deficientExpand
A New Protocol for the Consecutive α‐ and β‐Activation of Propiolates towards Electrophiles, Involving Conjugate Addition of Tertiary Amines and Intramolecular Silyl Migration
Herein, we present a novel approach for the consecutive alpha- and beta-activation of conjugated alkynes and demonstrate the application of this methodology towards the C-C bond-forming reactions ofExpand